| Record Information |
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| Version | 2.0 |
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| Created at | 2006-02-23 13:09:54 UTC |
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| Updated at | 2022-02-02 21:36:54 UTC |
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| NP-MRD ID | NP0000217 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Methanol |
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| Description | Methanol, also known as columbian spirit or CH3OH, belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl). The target of methanol in the eye is the retina, specifically the optic disk and optic nerve. Toxicity is due to the metabolic products of alcohol dehydrogenase (ADH) and aldehyde dehydrogenase. Methanol exists in all living organisms, ranging from bacteria to humans. Methanol is an alcoholic tasting compound. Outside of the human body, Methanol is found, on average, in the highest concentration within cow milk and sweet oranges. Methanol has also been detected, but not quantified in several different foods, such as prairie turnips, mountain yams, mentha (mint), watermelons, and pasta. Methanol is responsible for accidental, suicidal, and epidemic poisonings, resulting in death or permanent sequelae. Methanol is a potentially toxic compound. Visual disturbances develop between 18h to 48h after ingestion and range from mild photophobia and blurred vision to markedly reduced visual acuity and complete blindness. Methanol is metabolized to formaldehyde by alcohol dehydrogenase, then from that to formate by formaldehyde dehydrogenase, and then to carbon dioxide by limited H4 folate. It is the simplest alcohol, and is a light, volatile, colourless, flammable, poisonous liquid with a distinctive odor that is somewhat milder and sweeter than ethanol. |
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| Structure | InChI=1S/CH4O/c1-2/h2H,1H3 |
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| Synonyms | | Value | Source |
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| Carbinol | ChEBI | | CH3OH | ChEBI | | MeOH | ChEBI | | Methyl alcohol | ChEBI | | Methylalkohol | ChEBI | | Spirit OF wood | ChEBI | | Wood alcohol | ChEBI | | Wood naphtha | ChEBI | | Wood spirit | ChEBI | | Alcohol, methyl | HMDB | | Alcohol, wood | HMDB | | Methoxide, sodium | HMDB | | Sodium methoxide | HMDB | | Alcool methylique | HMDB | | Alcool metilico | HMDB | | Colonial spirit | HMDB | | Columbian spirit | HMDB | | Columbian spirits | HMDB | | Hydroxymethane | HMDB | | Metanolo | HMDB | | Methanol-water mixture | HMDB | | Methyl hydroxide | HMDB | | Methylol | HMDB | | Metylowy alkohol | HMDB | | Monohydroxymethane | HMDB | | Pyro alcohol | HMDB | | Pyroxylic spirit | HMDB |
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| Chemical Formula | CH4O |
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| Average Mass | 32.0419 Da |
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| Monoisotopic Mass | 32.02621 Da |
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| IUPAC Name | methanol |
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| Traditional Name | methanol |
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| CAS Registry Number | 67-56-1 |
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| SMILES | CO |
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| InChI Identifier | InChI=1S/CH4O/c1-2/h2H,1H3 |
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| InChI Key | OKKJLVBELUTLKV-UHFFFAOYSA-N |
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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, simulated) | Ahselim | | | 2022-03-29 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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| Species Where Detected | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl). |
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| Kingdom | Organic compounds |
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| Super Class | Organic oxygen compounds |
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| Class | Organooxygen compounds |
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| Sub Class | Alcohols and polyols |
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| Direct Parent | Primary alcohols |
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| Alternative Parents | |
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| Substituents | - Hydrocarbon derivative
- Primary alcohol
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State | Liquid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | -97.6 °C | Not Available | | Boiling Point | 64.00 to 65.00 °C. @ 760.00 mm Hg | The Good Scents Company Information System | | Water Solubility | 1000 mg/mL at 25 °C | Not Available | | LogP | -0.77 | Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995). |
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| Predicted Properties | |
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| General References | - Nagasawa H, Wada M, Koyama S, Kawanami T, Kurita K, Kato T: [A case of methanol intoxication with optic neuropathy visualized on STIR sequence of MR images]. Rinsho Shinkeigaku. 2005 Jul;45(7):527-30. [PubMed:16119839 ]
- Ferrari LA, Arado MG, Nardo CA, Giannuzzi L: Post-mortem analysis of formic acid disposition in acute methanol intoxication. Forensic Sci Int. 2003 Apr 23;133(1-2):152-8. [PubMed:12742704 ]
- Avella J, Briglia E, Harleman G, Lehrer M: Percutaneous absorption and distribution of methanol in a homicide. J Anal Toxicol. 2005 Oct;29(7):734-7. [PubMed:16419410 ]
- Bogdanov-Berezovsky A, Glesinger R, Kachko L, Arbel E, Rosenberg L, Grossman N: Accreditation of skin from a methanol-poisoned victim for banking and grafting. Transplantation. 2002 Jun 27;73(12):1913-7. [PubMed:12131687 ]
- Heinig K, Henion J: Determination of carnitine and acylcarnitines in biological samples by capillary electrophoresis-mass spectrometry. J Chromatogr B Biomed Sci Appl. 1999 Dec 10;735(2):171-88. [PubMed:10670733 ]
- Kaphalia BS, Carr JB, Ansari GA: Increased endobiotic fatty acid methyl esters following exposure to methanol. Fundam Appl Toxicol. 1995 Dec;28(2):264-73. [PubMed:8835236 ]
- Batterman SA, Franzblau A, Zhou N: Airborne emissions at skin surfaces: a potential biological exposure index. Int Arch Occup Environ Health. 1996;68(4):268-74. [PubMed:8738358 ]
- Vassiliadis J, Graudins A, Dowsett RP: Triethylene glycol poisoning treated with intravenous ethanol infusion. J Toxicol Clin Toxicol. 1999;37(6):773-6. [PubMed:10584590 ]
- Lee XP, Kumazawa T, Kondo K, Sato K, Suzuki O: Analysis of methanol or formic acid in body fluids by headspace solid-phase microextraction and capillary gas chromatography. J Chromatogr B Biomed Sci Appl. 1999 Oct 29;734(1):155-62. [PubMed:10574201 ]
- Jose N, Ajith TA, Janardhanan KK: Methanol extract of the oyster mushroom, Pleurotus florida, inhibits inflammation and platelet aggregation. Phytother Res. 2004 Jan;18(1):43-6. [PubMed:14750200 ]
- Comoglu S, Ozen B, Ozbakir S: Methanol intoxication with bilateral basal ganglia infarct. Australas Radiol. 2001 Aug;45(3):357-8. [PubMed:11531765 ]
- Yu C, Shin YG, Chow A, Li Y, Kosmeder JW, Lee YS, Hirschelman WH, Pezzuto JM, Mehta RG, van Breemen RB: Human, rat, and mouse metabolism of resveratrol. Pharm Res. 2002 Dec;19(12):1907-14. [PubMed:12523673 ]
- Keum YS, Park KK, Lee JM, Chun KS, Park JH, Lee SK, Kwon H, Surh YJ: Antioxidant and anti-tumor promoting activities of the methanol extract of heat-processed ginseng. Cancer Lett. 2000 Mar 13;150(1):41-8. [PubMed:10755385 ]
- Megarbane B, Borron SW, Baud FJ: Current recommendations for treatment of severe toxic alcohol poisonings. Intensive Care Med. 2005 Feb;31(2):189-95. Epub 2004 Dec 31. [PubMed:15627163 ]
- Purssell RA, Lynd LD, Koga Y: The use of the osmole gap as a screening test for the presence of exogenous substances. Toxicol Rev. 2004;23(3):189-202. [PubMed:15862085 ]
- Moon CS: Estimations of the lethal and exposure doses for representative methanol symptoms in humans. Ann Occup Environ Med. 2017 Oct 2;29:44. doi: 10.1186/s40557-017-0197-5. eCollection 2017. [PubMed:29026612 ]
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